Synthesis and biological evaluation of multivalent carbohydrate ligands obtained by click assembly of pseudo-rotaxanes

Multivalent carbohydrate ligands have been prepared by assembling alpha-cyclodextrin-based pseudo-rotaxanes through "click chemistry". The inclusion complex formed by a lactosyl-alpha-CD conjugate and a decane axle carrying a lactosyl stopper at one extremity and an azido group at the other end was dimerized by bis-propargyl spacers of different lengths to provide oligorotaxanes having adjustable threading ratios. For the first time, saccharidic ligands have been introduced on rotaxanes both as a biological recognition element and as a capping group. The supramolecular species have been isolated and characterized by mass spectrometry as well as by 1D and DOSY NMR experiments. Their ability to inhibit the binding of Arachis hypogaea agglutinin to asialofetuin, assayed by enzyme linked lectin assays (ELLA), was shown to be valency-dependent.